Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
  • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to a pyridinium salt and a pest control agent. More specifically, the present invention relates to a pyridinium salt which has excellent insecticidal activity and/or acaricidal activity, is excellent in safety and can be synthesized in an industrially favorable manner, and a pest control agent containing this pyridinium salt as an active ingredient.
• Patent Document 1 discloses a compound represented by formula (A) having acaricidal activity, and the like.
• Non-Patent Document 1 discloses a compound represented by formula (B) having analgesic activity, and the like.
• An object of the present invention is to provide a pyridinium salt which is excellent in pest control activity, in particular, insecticidal activity and/or acaricidal activity, excellent in safety and can be synthesized in an industrially favorable manner.
• Another object of the present invention is to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or an endoparasite control- or exterminating agent containing a pyridinium salt as an active ingredient.
• A represents an oxygen atom or a sulfur atom
• X 1 represents a halogeno group, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 2-6 alkenyl group, a substituted or unsubstituted C 2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C 1-6 alkoxy group, a substituted or unsubstituted C 2-6 alkenyloxy group, a substituted or unsubstituted C 2-6 alkynyloxy group, a substituted or unsubstituted C 1-6 alkylcarbonyl group, a substituted or unsubstituted C 1-6 alkoxycarbonyl group, a substituted or unsubstituted C 1-6 alkylthio group, a substituted or unsubstituted C 1-6 alkylsulfinyl group, a substituted or unsubstituted C 1-6 alkylsulfonyl
• n represents the number of X 1 and is any integer of 0 to 5;
• any two of X 1 may be bound together to form a bivalent hydrocarbon group
• Y represents a single bond or a substituted or unsubstituted C 2-6 alkenylene group
• Q 1 represents a substituted or unsubstituted C 6-10 arylene group or a substituted or unsubstituted 6- to 10-membered heteroarylene group;
• Q 2 represents a substituted or unsubstituted C 6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group;
• Z q ⁇ represents a counter ion; and q represents a valence of the counter ion and is 1 or 2.
• a pest control agent containing at least one compound selected from the compounds according to the above [1] as an active ingredient.
• An ectoparasite control agent containing at least one compound selected from the compounds according to the above [1] as an active ingredient.
• the pyridinium salt of the present invention has a function of controlling pests which are problematic in terms of agricultural crops and hygiene.
• a control agent containing the pyridinium salt of the present invention can effectively control pests, particularly agricultural pests and mites and ticks at a lower concentration, and can also effectively control ectoparasites and endoparasites that may harm humans and animals.
• a pyridinium salt of the present invention is a compound (inner salt) represented by formula (I) or a compound (intermolecular salt) represented by formula (II).
• An inner salt is a compound having a cation center and an anion center in one molecule, that is, a zwitterion.
• An intermolecular salt is a compound formed by ion association of a cation and an anion, that is, an ion pair.
• unsubstituted means that it is composed only of a group which becomes a mother nucleus. When it is described only by the name of the group which becomes the mother nucleus without being described as “substituted”, it means “unsubstituted” unless otherwise stated.
• substituted means that any hydrogen atom of the group which is to become the mother nucleus is substituted with a group (substituent) having the same or different structure as that of the mother nucleus. Therefore, a “substituent” is another group bonded to the group which becomes the mother nucleus.
• the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
• C 1-6 and the like mean that the number of carbon atoms in the group which becomes the mother nucleus is 1 to 6, and so on.
• the number of carbon atoms does not include the number of carbon atoms present in the substituent.
• a butyl group having an ethoxy group as a substituent is classified as a C 2 alkoxy C 4 alkyl group.
• a “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
• groups which can be a “substituent” are exemplified.
• a C 1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group;
• a C 2-6 alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group;
• a C 2-6 alkynyl group such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group;
• a C 3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and cubanyl group;
• a C 6-10 aryl group such as a phenyl group and a naphthyl group
• a C 6-10 aryl C 1-6 alkyl group such as a benzyl group and a phenethyl group
• a C 1-6 alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group;
• a C 2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;
• a C 2-6 alkynyloxy group such as an ethynyloxy group and a propargyloxy group
• a C 6-10 aryloxy group such as a phenoxy group and a naphthoxy group
• a C 6-10 aryl C 1-6 alkoxy group such as a benzyloxy group and a phenethyloxy group
• a 5- to 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group
• a 5- to 6-membered heteroaryl C 1-6 alkyloxy group such as a thiazolylmethyloxy group and a pyridylmethyloxy group
• a C 1-6 alkylcarbonyl group such as an acetyl group and a propionyl group
• a C 1-6 alkylcarbonyloxy group such as an acetyloxy group and a propionyloxy group
• a C 6-10 arylcarbonyl group such as a benzoyl group
• a C 1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group;
• a C 1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group and a t-butoxycarbonyloxy group;
• halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group
• a C 1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group;
• a C 2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;
• a C 2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group;
• a C 1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group;
• a C 2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;
• a C 1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group and a trichloroacetyl group;
• a C 1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group and a diethylamino group;
• a C 6-10 arylamino group such as an anilino group and a naphthylamino group
• a C 6-10 aryl C 1-6 alkylamino group such as a benzylamino group and a phenethylamino group
• a C 1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group and an i-propylcarbonylamino group;
• a C 1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group and an i-propoxycarbonylamino group;
• an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group and an N-phenyl-N-methylaminocarbonyl group;
• an imino C 1-6 alkyl group such as an iminomethyl group, a (1-imino)ethyl group and a (1-imino)-n-propyl group;
• N-hydroxyimino C 1-6 alkyl group such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, and a (1-(N-methoxy)-imino)ethyl group;
• a C 1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group, and a dimethylaminocarbonyloxy group;
• a C 1-6 alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group and a t-butylthio group;
• a C 1-6 haloalkylthio group such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group
• a C 6-10 arylthio group such as a phenylthio group and a naphthylthio group
• a 5- to 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group
• a C 1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group;
• a C 1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;
• a C 6-10 arylsulfinyl group such as a phenylsulfinyl group
• a 5- to 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group;
• a C 1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group;
• a C 1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;
• a C 6-10 arylsulfonyl group such as a phenylsulfonyl group
• a 5- to 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;
• a C 1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group and a t-butylsulfonyloxy group;
• a C 1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group;
• a tri C 1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group and a t-butyldimethylsilyl group;
• a tri C 6-10 aryl-substituted silyl group such as a triphenylsilyl group
• any hydrogen atom in the substituent may be substituted with a group having a different structure.
• the “substituent” in this case include a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a halogeno group, a cyano group and a nitro group.
• the above-described “3- to 6-membered heterocyclyl group” includes 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
• the heterocyclyl group may be either monocyclic or polycyclic. As long as the polycyclic heterocyclyl group includes at least one heterocyclic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring.
• Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
• Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
• Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
• 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
• Z q ⁇ represents a counter ion
• q represents a valence of the counter ion and is 1 or 2.
• a monovalent anion Z ⁇ include Cl ⁇ , Br ⁇ , I ⁇ , NO 3 ⁇ , CH 3 COO ⁇ , CH 3 SO 3 ⁇ , CF 3 SO 3 ⁇ and TolSO 3 ⁇ .
• a bivalent anion Z 2 ⁇ include SO 4 2 ⁇ and the like.
• Tol is an abbreviation indicating an o-methylphenyl group, an m-methylphenyl group or a p-methylphenyl group.
• A represents an oxygen atom or a sulfur atom.
• A is preferably an oxygen atom.
• X 1 represents a halogeno group, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 2-6 alkenyl group, a substituted or unsubstituted C 2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C 1-6 alkoxy group, a substituted or unsubstituted C 2-6 alkenyloxy group, a substituted or unsubstituted C 2-6 alkynyloxy group, a substituted or unsubstituted C 1-6 alkylcarbonyl group, a substituted or unsubstituted C 1-6 alkoxycarbonyl group, a substituted or unsubstituted C 1-6 alkylthio group, a substituted or unsubstituted C 1-6 alkylsulfinyl group, a substituted or unsubstituted C
• m represents the number of X t and is any integer of 0 to 5;
• any two of X 1 may be bound together to form a bivalent hydrocarbon group.
• halogeno group represented by X 1
• a fluoro group a chloro group, a bromo group, an iodo group and the like can be mentioned.
• the “C 1-6 alkyl group” represented by X 1 may be linear or branched.
• the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group.
• Examples of the “C 2-6 alkenyl group” represented by X 1 include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group and a 5-hexenyl group.
• Examples of the “C 2-6 alkynyl group” represented by X 1 include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group and a 1,1-dimethyl-2-butynyl group.
• Examples of the “C 1-6 alkoxy group” represented by X 1 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group and an i-hexyloxy group.
• Examples of the “C 2-6 alkenyloxy group” represented by X 1 include a vinyloxy group, an allyloxy group, a propenyloxy group and a butenyloxy group.
• Examples of the “C 2-6 alkynyloxy group” represented by X 1 include an ethynyloxy group and a propargyloxy group.
• Examples of the “C 1-6 alkylcarbonyl group” represented by X 1 include an acetyl group and a propionyl group.
• Examples of the “C 1-6 alkoxycarbonyl group” represented by X 1 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group and a t-butoxycarbonyl group.
• Examples of the “C 1-6 alkylthio group” represented by X′ include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group.
• Examples of the “C 1-6 alkylsulfinyl group” represented by X 1 include a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group.
• Examples of the “C 1-6 alkylsulfonyl group” represented by X 1 include a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group.
• Examples of the “C 1-6 alkylsulfonyloxy group” represented by X 1 include a methylsulfonyloxy group, an ethylsulfonyloxy group and a t-butylsulfonyloxy group.
• Examples of the “C 1-6 alkylamino group” represented by X 1 include a mono C 1-6 alkylamino group such as a methylamino group and an ethylamino group; and a di C 1-6 alkylamino group such as a dimethylamino group and a diethylamino group.
• Examples of the “C 3-8 cycloalkyl group” represented by X 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group.
• Examples of the “C 3-8 cycloalkyloxy group” represented by X 1 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and a cycloheptyloxy group.
• Examples of the “C 6-10 aryl group” represented by X 1 include a phenyl group and a naphthyl group.
• Examples of the “C 6-10 aryloxy group” represented by X 1 include a phenoxy group and a naphthoxy group.
• the “5- to 6-membered heteroaryl group” represented by X 1 contains 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
• Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group, and examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
• the “5- to 6-membered heteroaryloxy group” represented by X 1 is a structure in which a 5- or 6-membered heteroaryl group and an oxy group are bonded. Specific examples thereof include a thiazolyloxy group and a pyridyloxy group.
• Preferred examples of the substituents on the “C 3-8 cycloalkyl group”, “C 3-5 cycloalkyloxy group”, “C 6-10 aryl group”, “C 6-10 aryloxy group”, “5- to 6-membered heteroaryl group” or “5- to 6-membered heteroaryloxy group” represented by X 1 include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6 haloalkyl group such as a chloromethyl group, a chloroethyl
• Examples of the “bivalent hydrocarbon group” formed by any two of X 1 together include a trimethylene group, a tetramethylene group, a vinylene group and a 1,3-butadiene-1,4-diyl group.
• X 1 is preferably a halogeno group, a halogeno group-substituted or unsubstituted C 1-6 alkyl group, or a halogeno group-substituted or unsubstituted C 1-6 alkoxy group.
• X 1 is a halogeno group-substituted C 1-6 alkyl group
• specific examples thereof include a C 1-6 haloalkyl group such as a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and a 2,2,2,1,1-pentafluoroethyl group.
• X 1 is a halogeno group-substituted C 1-6 alkoxy group
• specific examples thereof include a C 1-6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,1,1-tetrafluoroethoxy group and a 2,2,2,1,1-pentafluoroethoxy group.
• Q 2 represents a substituted or unsubstituted C 6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.
• Examples of the “C 6-10 aryl group” represented by Q 2 include a phenyl group and a naphthyl group.
• Examples of the “5- to 6-membered heteroaryl group” represented by Q 2 include a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group; and a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
• a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imi
• Examples of the substituent on the “C 6-10 aryl group” or “5- to 6-membered heteroaryl group” represented by Q 2 include a halogeno group, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 2-6 alkenyl group, a substituted or unsubstituted C 2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C 1-6 alkoxy group, a substituted or unsubstituted C 2-6 alkenyloxy group, a substituted or unsubstituted C 2-6 alkynyloxy group, a substituted or unsubstituted C 1-6 alkylcarbonyl group, a substituted or unsubstituted C 1-6 alkoxycarbonyl group, a substituted or unsubstituted C 1-6 alkylthio group, a substituted or unsubstituted C 1-6 alkyl
• any two substituents may form a bivalent organic group together.
• a halogeno group a halogeno group-substituted or unsubstituted C 1-6 alkyl group, a halogeno group-substituted or unsubstituted C 2-6 alkynyl group, a hydroxyl group, a halogeno group-substituted or unsubstituted C 1-6 alkoxy group, a substituted or unsubstituted benzyl group, a halogeno group-substituted or unsubstituted C 1-6 alkoxycarbonyl group, a halogeno group-substituted or unsubstituted C 1-6 alkylthio group, a halogeno group-substituted or unsubstituted C 1-6 alkylsulfonyl group, a
• substituent on the “C 6-10 aryl group” or “5- to 6-membered heteroaryl group” represented by Q 2 is a halogeno group-substituted C 1-6 alkyl group
• specific examples thereof include a C 1-6 haloalkyl group such as a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2,1,1-pentafluoroethyl group and a 3,3,3,2,2,1,1-heptafluoropropyl group.
• the substituent on the “C 6-10 aryl group” or “5- to 6-membered heteroaryl group” represented by Q 2 is a halogeno group-substituted C 1-6 alkoxy group
• specific examples thereof include a C 1-6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,1,1-tetrafluoroethoxy group, a 2,2,2,1,1-pentafluoroethoxy group, a 3,3,2,2-tetrafluoropropoxy group, a 3,3,3,2,2-pentafluoropropoxy group, a 3,3,3,2,1,1-hexafluoropropyloxy group and a 4,4,4,3,3,2,2-heptafluorobutoxy group.
• the substituent on the “C 6-10 aryl group” or “5- to 6-membered heteroaryl group” represented by Q 2 is a substituted benzyl group
• the substituent on the benzyl group is preferably a halogeno group, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group or a C 1-6 haloalkoxy group.
• the substituent on the “C 6-10 aryl group” or “5- to 6-membered heteroaryl group” represented by Q 2 is a substituted phenyl group
• the substituent on the phenyl group is preferably a halogeno group, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group or a C 1-6 haloalkoxy group.
• Examples of the “bivalent organic group” formed by any two of the substituents together include a trimethylene group, a tetramethylene group, a vinylene group and a 1,3-butadiene-1,4-diyl group.
• Y represents a single bond or a substituted or unsubstituted C 2-6 alkenylene group.
• Examples of the “C 2-6 alkenylene group” represented by Y include a vinylene group, a propenylene group and a butenylene group.
• Examples of the substituent on the “C 2-6 alkenylene group” represented by Y include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group and a t-butyl group; a C 1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6 alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-prop
• the substituent on the “C 2-6 alkenylene group” represented by Y is preferably a halogeno group, a halogeno group-substituted or unsubstituted C 1-6 alkyl group, or a halogeno group-substituted or unsubstituted C 1-6 alkoxy group.
• Q 1 represents a substituted or unsubstituted C 6-10 arylene group or a substituted or unsubstituted 6- to 10-membered heteroarylene group.
• Examples of the “C 6-10 arylene group” represented by Q 1 include a phenylene group such as a 1,2-phenylene group, a 1,3-phenylene group and a 1,4-phenylene group, and a naphthylene group such as a 2,6-naphthylene group.
• Examples of the “6- to 10-membered heteroarylene group” represented by Q 1 include a 6-membered heteroarylene group such as a pyridylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group and a triazinylene group; an indolediyl group such as a 1H-indole-2,6-diyl group; a benzofurandiyl group such as a benzo [b] furan-2,6-diyl group; a benzothiophenediyl group such as a benzo [b] thiophene-2,6-diyl group; a benzoxazolediyl group such as a benzoxazole-2,5-diyl group and a benzoxazole-2,6-diyl group; a 9-membered heteroarylene group such as a benzothiazolediyl group such as
• Examples of the substituent X 2 on the “C 6-10 arylene group” or “6- to 10-membered heteroarylene group” represented by Q 1 include a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group; a C 1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group and a t-butyl group; a C 1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6 alkoxy group such as a methoxy group, an e
• Q 1 is preferably a substituted or unsubstituted 1,4-phenylene group, a substituted or unsubstituted 1H-indolediyl group, a substituted or unsubstituted 1-benzofurandiyl group, a substituted or unsubstituted 1-benzothiophenediyl group, a substituted or unsubstituted 1,3-benzoxazolediyl group, a substituted or unsubstituted 1,3-benzothiazolediyl group and a 1H-benzimidazolediyl group.
• the substituent X 2 is preferably a halogeno group, a halogeno group-substituted or unsubstituted C 1-6 alkyl group, a halogeno-substituted or unsubstituted C 1-6 alkoxy group, or a nitro group.
• preferred pyridinium salts of the present invention include compounds represented by formula (I-a) or formula (II-a); compounds represented by formula (I-b) or formula (II-b); and compounds represented by formula (I-c) or formula (II-c).
• X 2 and n in the formulas (I-a), (II-a), (I-b), (II-b), (I-c) and (II-c) are the same as the substituent X 2 on the “C 6-10 arylene group” or “6- to 10-membered heteroarylene group” represented by Q 1 and the number n thereof.
• a 1 represents a nitrogen atom, a group represented by CH or a group represented by CX 2
• a 2 represents an oxygen atom, a sulfur atom, a group represented by NH, or a group represented by NX 2
• X 2 is the same as the substituent X 2 on the “C 6-10 arylene group” or “6- to 10-membered heteroarylene group” represented by Q′.
• the pyridinium salt of the present invention is not particularly limited by its production method.
• the pyridinium salt of the present invention (hereinafter sometimes referred to as the “compound of the present invention”) can be obtained using a known reaction described in Examples and the like.
• the compound of the present invention is excellent in the effect of controlling harmful organisms such as various agricultural pests affecting the growth of plants, and mites and ticks.
• the compound of the present invention is a highly safe material because it has less phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.
• the compound of the present invention exhibits an excellent controlling effect not only on susceptible strains but also on various resistant strains of insect pests and acaricide-resistant strains of mites and ticks.
• the compound of the present invention is excellent in the effect of controlling ectoparasites and endoparasites which harm humans and animals. In addition, it is a highly safe material because of its low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an agent for controlling ectoparasites and endoparasites.
• the compound of the present invention shows efficacy in all developmental stages of organisms to be controlled, and shows excellent control effect, for example, on eggs, nymphs, larvae, pupae and adults of mites and ticks, insects and the like.
• the pest control agent or the insecticidal or acaricidal agent of the present invention contains at least one selected from the pyridinium salts of the present invention as an active ingredient.
• the amount of the compound of the present invention contained in the pest control agent or the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it shows the effect of controlling harmful organisms, agricultural pests or mites and ticks.
• the pest control agent or the insecticidal or acaricidal agent of the present invention is preferably used for grains; vegetables; root vegetables; potatoes; flowers and ornamental plants; fruit trees; foliage plants and trees of tea, coffee, cacao and the like; pasture grasses; turf grasses; and plants such as cotton.
• the pest control agent or the insecticidal or acaricidal agent of the present invention may be used to any portions of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings and the like.
• the pest control agent or the insecticidal or acaricidal agent of the present invention is not particularly limited depending on the species of the plant to be applied.
• the plant species include an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid and a genetically modified organism (GMO).
• the pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application and the like, in order to control various agricultural pests and mites and ticks.
• Arctiidae moths for example, Hyphantria cunea and Lemyra imparilis;
• Carposinidae for example, Carposina sasakii
• Thysanoptera Insect Pests (a) Phlaeothripidae, for example, Ponticulothrips diospyrosi ; and (b) Thripidae, for example, Frankliniella intonsa and Frankliniella occidentalis of Frankliniella spp.; Thrips palmi and Thrips tabaci of Thrips spp.; and others such as Heliothrips haemorrhoidalis and Scirtothrips dorsalis.
• Clypeorrhyncha (a) Cicadellidae, for example, Empoasca fabae, Empoasca nipponica, Empoasca onukii and Empoasca sakaii of Empoasca spp.; and others such as Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons and Nephotettix cinctinceps.
• C Heteroptera
• Alydidae for example, Riptortus clavatus
• Coreidae for example, Cletus punctiger and Leptocorisa chinensis
• Lygaeidae for example, Blissus leucopterus, Cavelerius saccharivorus and Togo hemipterus
• Miridae for example, Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus and Trigonotylus caelestialium
• Pentatomidae for example, Nezara antennata and Nezara viridula of Nezara spp.
• Eysarcoris aeneus Eysarcoris lewisi and Eysarcoris ventralis of Eysarcoris spp.
• (D) Sternorrhyncha (a) Adelgidae, for example, Adelges laricis; (b) Aleyrodidae, for example, Bemisia argentifolii and Bemisia tabaci of Bemisia spp.; and others such as Aleurocanthus spiniferus, Dialeurodes citri and Trialeurodes vaporariorum; (c) Aphididae, for example, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi, Aphis sambuci and Aphis spiraecola of Aphis spp.; Rhopalosiphum maidis and Rhopalosiphum padi of Rhopalosiphum spp.; Dysaphis plantaginea and Dysaphis radicola of Dysaphis spp.; Macrosiphum avena
• Agromyzidae for example, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae and Liriomyza trifolii of Liriomyza spp.; and others such as Chromatomyia horticola and Agromyza oryzae;
• Anthomyiidae for example, Delia platura and Delia radicum of Delia spp.; and others such as Pegomya cunicularia;
• Drosophilidae for example, Drosophila melanogaster and Drosophila suzukii of Drosophila spp.;
• Ephydridae for example, Hydrellia griseola;
• Psilidae for example, Psila rosae ; and
• Tephritidae for example,
• Nematocera (a) Cecidomyiidae, for example, Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor and Sitodiplosis mosellana.
• Orthoptera Insect Pests (a) Acrididae, for example, Schistocerca americana and Schistocerca gregaria of Schistocerca spp.; and others such as Chortoicetes terminifera, Dociostaurus maroccanus, Locusta migratoria, Locustana pardalina, Nomadacris septemfasciata and Oxya yezoensis; (b) Gryllidae, for example, Acheta domestica and Teleogryllus emma; (c) Gryllotalpidae, for example, Gryllotalpa orientalis ; and (d) Tettigoniidae, for example, Tachycines asynamorus.
• Acrididae for example, Schistocerca americana and Schistocerca gregaria of Schistocerca spp.
• others such as Chortoicetes terminifera, Dociostaurus maroccanus, Locusta migratori
• Acari (A) Acaridida of Astigmata (a) Acaridae mites, for example, Rhizoglyphus echinopus and Rhizoglyphus robini of Rhizoglyphus spp.; Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae and Tyrophagus similis of Tyrophagus spp.; and others such as Acarus siro, Aleuroglyphus ovatus and Mycetoglyphus fungivorus; (B) Actinedida of Prostigmata (a) Tetranychidae mites, for example, Bryobia praetiosa and Bryobia rubrioculus of Bryobia spp.; Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetran
• the pest control agent of the present invention may be mixed with or used in combination with other active ingredients such as fungicides, insecticidal and acaricidal agents, nematicides and soil pesticides; plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like.
• active ingredients such as fungicides, insecticidal and acaricidal agents, nematicides and soil pesticides; plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like.
• a combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect on insecticidal, acaricidal and nematicidal activities.
• the synergistic effect can be confirmed by the Colby's formula (Colby, S. R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, 20-22, 1967) according to a conventional method.
• insecticides include miticides, nematicides, soil pesticides, and parasiticides and the like that can be mixed or used in combination with the pest control agent of the present invention are listed below.
• GABA receptor chloride ion channel antagonists acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, and dienochlor.
• Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, and flupyrimin
• Nicotinic acetylcholine receptor allosteric modulators spinetoram and spinosad.
• Chloride channel activators abamectin, emamectin-benzoate, lepimectin, milbemectin, ivermectin, seramectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, and nemadectin.
• Juvenile hormone-like substances hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, and triprene.
• Oxidative phosphorylation uncoupling agents chlorfenapyr, sulfluramid, DNOC, binapacryl, dinobuton, and dinocap.
• Nicotinic acetylcholine receptor channel blockers bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium, and thiocyclarm.
• Chitin synthesis inhibitors bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, novifumuron, teflubenzuron, triflumuron, buprofezin, and fluazuron.
• Diptera molting disturbing agent cyromazine.
• Molting hormone receptor agonists chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
• Octopamine receptor agonists amitraz, demiditraz, and chlordimeform
• Mitochondria electron transfer chain complex III inhibitors acequinocyl, fluacrypyrim, hydramethylnon, and bifenazate.
• Mitochondria electron transfer chain complex I inhibitors fenazaquin, fenproximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone.
• Voltage-dependent sodium channel blockers indoxacarb and metaflumizone.
• Acetyl CoA carboxylase inhibitors spirodiclofen, spiromesifen, spirotetramat, and spiropidion.
• Mitochondria electron transfer chain complex IV inhibitors aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, and cyanide.
• Mitochondria electron transfer chain complex II inhibitors cyenopyrafen, cyflumetofen, and pyflubumide.
• Ryanodine receptor modulators chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, and tetraniliprole.
• Parasiticides (a) Benzimidazole-based: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, and cambendazole; (b) Salicylanilide-based: closantel, oxyclozanide, rafoxanide, and niclosamide; (c) Substituted phenol-based: nitroxinil, nitroscanate; (d) Pyrimidine-based: pyrantel and morantel; (e) Imidazothiazole-based: levamisole and tetramisole; (f) Tetrahydropyrimidine-based: praziquantel and epsiprantel; and (g) Other parasiticides: cyclodiene, ryania,
• fungicides that can be mixed or used in combination with the pest control agent of the present invention are listed below.
• RNA polymerase I inhibitors benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, and ofurace;
• Adenosine deaminase inhibitors bupirimate, dimethirimol, and ethirimol;
• ⁇ -tubulin polymerization inhibitors benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, and ethaboxam;
• Signal transduction inhibitors (a) Signal transduction inhibitors: quinoxyfen and proquinazid; and (b) MAP/histidine kinase inhibitors in osmotic pressure signal transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, and vinclozolin.
• Lipid and cell membrane synthesis inhibitors (a) Phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, and isoprothiolane; (b) Lipid peroxidation agents: biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl, and etridiazole; (c) Agents that act upon cell membranes: iodocarb, propamocarb, propamocarb-hydrochloride, propamocarb-fosetylate, and prothiocarb; (d) Microorganisms that disturb pathogen cell membranes: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, and Bacillus subtilis strain D747; and (e) Agents that disturb cell membranes: Melaleuca alternifoli
• Cell membrane sterol biosynthesis inhibitors (a) C14 position demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil-sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobut
• Cell wall synthesis inhibitors (a) Trehalase inhibitor: validamycin; (b) Chitin synthase inhibitors: polyoxins and polyoxorim; and (c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, iprovalicarb, tolprocarb, valifenalate, and mandipropamide. (9) Melanin biosynthesis inhibitors: (a) Reductase inhibitors in melanin biosynthesis: fthalide, pyroquilon, and tricyclazole; and (b) Anhydrase inhibitors in melanin biosynthesis: carpropamid, diclocymet, and fenoxanil.
• Host plant resistance-inducing agents (a) Agent that acts on salicylic acid biosynthetic pathway: acibenzolar-S-methyl, and (b) Others: probenazole, tiadinil, isotianil, laminarin, and Reynoutria sachalinensis extract.
• Agents for which the mode of activity is unclear cymoxanil, fosetyl-aluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, dodine free base, and flutianil
• Agents having multiple activities copper (copper salts), bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminocta
• plant growth regulators that can be mixed or used in combination with the pest control agent of the present invention are listed below.
• the ectoparasite control agent of the present invention contains at least one selected from the pyridinium salts of the present invention as an active ingredient.
• the amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as it shows the effect of controlling ectoparasites.
• Examples of host animals to be treated with the ectoparasite control agent of the present invention include warm-blooded animals including pet animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs and sheep; domestic fowls; and the like.
• warm-blooded animals including pet animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs and sheep; domestic fowls; and the like.
• honey bees, stag beetles and beetles can be exemplified.
• the ectoparasite control agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration).
• a method therefor a method of orally administering tablets, capsules, mixed feeds or the like to the animals; a method of administering to the animals by using an immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal or the like) or the like; a method of topically administering by spraying, pouring-on or spotting-on an oily or aqueous liquid preparation; a method of kneading an ectoparasite control agent in a resin, molding the kneaded product into an appropriate shape such as a collar, ear tag or the like, and attaching and topically administering the resultant to the animals; and the like can be mentioned.
• Ectoparasites are parasitic in and on host animals, especially warm-blooded animals. More specifically, the ectoparasites are parasitic in and on the back, armpit, lower abdomen, inner thigh and the like of the host animals and obtain nutritional sources such as blood and dandruff from the animals to live. Examples of ectoparasites include mites and ticks, lice, fleas, mosquitoes, stable flies, flesh flies and the like.
• Mites belonging to the family Dermanyssidae mites belonging to the family Cellyssidae, mites belonging to the family Laelapidae, mites belonging to the family Varroidae, mites belonging to the family Argasidae, mites belonging to the family Ixodidae, mites belonging to the family Psoroptidae, mites belonging to the family Sarcoptidae, mites belonging to the family Knemidokoptidae, mites belonging to the family Demodixidae, mites belonging to the family Trombiculidae, insect-parasitic mites such as Coleopterophagus berlesei or the like.
• Fleas of the family Pulicidae for example, species belonging to the genus Ctenocephalides ( Ctenocephalides spp.) such as Ctenocephalides canis and Ctenocephalides felis;
• the endoparasite control- or exterminating agent of the present invention contains at least one selected from the pyridinium salts of the present invention as an active ingredient.
• the amount of the compound of the present invention contained in the endoparasite control- or exterminating agent of the present invention is not particularly limited as long as it shows the effect of controlling endoparasites.
• the parasite to be targeted by the endoparasite control- or exterminating agent of the present invention is parasitic (endoparasitic) in host animals, especially warm blooded animals and fish.
• host animals for which the endoparasite control- or exterminating agent of the present invention is effective include warm-blooded animals such as humans, domestic mammals (for example, cattle, horses, pigs, sheep, goats and the like), laboratory animals (for example, mice, rats, gerbils and the like), pet animals (for example, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, and the like), wild and zoo mammals (monkeys, foxes, deers, buffaloes and the like), domestic fowls (turkeys, ducks, chickens, quails, geese and the like) and pet birds (pigeons, parrots, hill mynas, Java sparrows, parakeets, society finches, canaries and
• Examples of parasites that can be controlled or exterminated include those listed below.
• Kidney worms of the Dioctophymatidae family for example, Dioctophyma renale of Dioctophyma spp.;
• Kidney worms of the Soboliphymatidae family for example, Soboliphyme abei and Soboliphyme baturini of Soboliphyme spp.
• Trichina worms of the Trichinellidae family for example, Trichinella spiralis of Trichinella spp.
• Whipworms of the Trichuridae family for example, Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica and Capillaria suis of Capillaria spp.; and Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini and Trichuris suis of Trichuris spp.
• Threadworms of the Strongyloididae family for example, Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens and Strongyloides ratti of Strongyloides spp.
• Hookworms of the Ancylostomatidae family for example, Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale and Ancylostoma tubaeforme of Ancylostoma spp.; Uncinaria stenocephala of Uncinaria spp.; and Bunostomum phlebotomum and Bunostomum trigonocephalum of Bunostomum spp.
• Nematodes of the Angiostrongylidae family for example, Aelurostrongylus abstrusus of Aelurostrongylus spp.; and Angiostrongylus vasorum and Angiostrongylus cantonesis of Angiostrongylus spp.;
• Gapeworms of the Syngamidae family for example, Cyathostoma bronchialis of Cyathostoma spp.; and Syngamus skrjabinomorpha and Syngamus trachea of Syngamus spp.
• Nematodes of the Molineidae family for example, Nematodirus filicollis and Nematodirus spathiger of Nematodirus spp.;
• Nematodes of the Dictyocaulidae family for example, Dictyocaulus filarial and Dictyocaulus viviparus of Dictyocaulus spp.;
• Nematodes of the Haemonchidae family for example, Haemonchus contortus of Haemonchus spp.; and Mecistocirrus digitatus of Mecistocirrus spp.;
• Nematodes of the Heligmonellidae family for example, Nippostrongylus braziliensis of Nippostrongylus spp.;
• Nematodes of the Trichostrongylidae family for example, Trichostrongylus axei, Trichostrongylus colubriformis and Trichostrongylus tenuis of Trichostrongylus spp.; Hyostrongylus rubidus of Hyostrongylus spp.; and Obeliscoides cuniculi of Obeliscoides spp.
• Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, Chabertia ovina of Chabertia spp.; and Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum and Oesophagostomum watanabei of Oesophagostomum spp.; (b) Nematodes of the Stephanuridae family, for example, Stephanurus dentatus of Stephanurus spp.; and (c) Nematodes of the Strongylidae family, for example, Strongylus as
• Oxyurida nematodes Nematodes of the Oxyuridae family, for example, Enterobius anthropopitheci and Enterobius vermicularis of Enterobius spp.; Oxyuris equi of Oxyuris spp.; and Passalurus ambiguus of Passalurus spp.
• Ascaridida nemtaodes (a) Nematodes of the Ascaridiidae family, for example, Ascaridia galli of Ascaridia spp.; (b) Nematodes of the Heterakidae family, for example, Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla and Heterakis putaustralis of Heterakis spp.; (c) Nematodes of the Anisakidae family, for example, Anisakis simplex of Anisakis spp.; (d) Nematodes of the Ascarididae family, for example, Ascaris lumbricoides and Ascaris suum of Ascaris spp.; and Parascaris equorum of Parascaris spp.; and (e) Nematodes of the Toxocaridae family, for example, Toxocara canis, Toxocar
• Spirurida nematodes (a) Nematodes of the Onchocercidae family, for example, Brugia malayi, Brugia pahangi and Brugia patei of Brugia spp.; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of Dirofilaria spp.; Filaria oculi of Filaria spp.; and Onchocerca cervicalis, Onchocerca gibsoni and Onchocerca gutturosa of Onchocerca spp.
• Nematodes of the Setariidae family for example, Setaria digitata, Setaria equina, Setaria labiatopapillosa and Setaria marshalli of Setaria spp.; and Wuchereria bancrofti of Wuchereria spp.; and
• Nematodes of the Filariidae family for example, Parafilaria multipapillosa of Parafilaria spp.; and Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis and Stephanofilaria stilesi of Stephanofilaria spp.
• Spirurida nematodes (a) Nematodes of the Gnathostomatidae family, for example, Gnathostoma doloresi and Gnathostoma spinigerum of Gnathostoma spp.; (b) Nematodes of the Habronematidae family, for example, Habronema majus, Habronema microstoma and Habronema muscae of Habronema spp.; and Draschia megastoma of Draschia spp.; (c) Nematodes of the Physalopteridae family, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Phys
• the compounds of the present invention are excellent in the effect of controlling insect pests having a stinger or venom which harm humans and animals, insect pests that mediate various pathogens/pathogenic microbes, and insect pests that cause discomfort to humans (such as toxic pests, hygiene pests and unpleasant pests).
• Sawflies of the Argidae family wasps of the Cynipidae family, sawflies of the Diprionidae family, ants of the Formicidae family, wasps of the Mutillidae vamily family, and wasps of the Vespidae family.
• Blattodea termites, Araneae, centipedes, millipedes, crustacea and Cimex lectularius.
• 10 parts of the compound of the present invention 4 parts of a polyoxyethylene alkyl allyl ether, 2 parts of a polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed and subjected to wet grinding until the particle size becomes 3 microns or less to obtain a suspension containing 10% of an active ingredient.
• 0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter.
• the resultant was extracted with 2N hydrochloric acid, and a 10% sodium hydroxide aqueous solution was added to the obtained aqueous layer until the pH reached 11.
• the resultant was extracted with chloroform, washed with water and then dried over anhydrous magnesium sulfate. The chloroform was distilled off to obtain the desired product (0.09 g).
• 1-aminopyridinium iodide was prepared by the method described in Organic Syntheses Collective Volume V. p. 43 (1973).
• Examples of the compounds of the present invention prepared by the same method as in the above Examples are shown in Tables 1 to 4.
• Physical property data of the compounds were entered in the column of “Physical properties”. As the physical property data, properties or melting points (m.p.) were described.
• Me represents a methyl group
• Ph represents a phenyl group
• i Pr represents an i-propyl group
• t Bu represents a t-butyl group
• Et represents an ethyl group.
• Table 1 shows the compounds represented by the formula (I-a) among the compounds of the present invention.
• the bond marked with the symbol * used for the notation of Y is bonded to the carbonyl group in the pyridinium salt.
• Table 2 shows the compounds represented by formula (I′). The bond marked with the symbol * used for the notation of Q 1 -Q 2 is bonded to the carbonyl group in the pyridinium salt.
• Table 3 shows the compounds represented by the formula (II-a). The bond marked with the symbol * used for the notation of Y is bonded to the carbonyl group in the pyridinium salt.
• “Tol” represents a tolyl group.
• Table 4 shows the compounds represented by formula (I-a′).
• Parts are on a weight basis.
• the emulsion (1) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Maize leaf pieces were immersed in the diluent for 30 seconds. The maize leaf pieces were placed in a petri dish, and five second instar larvae of M. separata were released.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated when 6 days passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds shown in Table 5 were tested for efficacy against M. separata . All compounds showed an insecticidal rate of 80% or more against M. separata .
• the insecticidal rate of the compound represented by formula (A) (sometimes referred to as comparative compound A) described in Patent Document 1 was 0%.
• the emulsion (1) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• Cabbage leaves were immersed in the diluent for 30 seconds.
• the cabbage leaves were placed in a petri dish, and five second instar larvae of S. litura were released.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated when 6 days passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds shown in Table 6 were tested for efficacy against S. litura . All compounds showed an insecticidal rate of 80% or more against S. litura . The insecticidal rate of the comparative compound A was 0%.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• Cabbage leaves were immersed in the diluent for 30 seconds.
• the cabbage leaves were air dried and placed in a petri dish, and five second instar larvae of P. xylostella were released.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated when 3 days passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds with compound numbers shown in Table 7 were tested for efficacy against P. xylostella . All compounds showed an insecticidal rate of 80% or more against P. xylostella . The insecticidal rate of the comparative compound A was 0%.
• Kidney bean plants were raised in No. 3 pots, and 8 adult females of T. urticae from Aomori Prefecture were inoculated on primary leaves.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• the diluent was sprayed on the kidney bean plants (treated group).
• the emulsion (11) was diluted 400 times with water.
• the diluent was sprayed on the kidney bean plants (untreated group).
• Nt number of surviving individuals in treated group
• Nc number of surviving individuals in untreated group
• the compounds with compound numbers shown in Table 8 were tested for efficacy against T. urticae . All compounds showed a control rate of 90% or more. The control rate of the comparative compound A was 100%.
• 1% agar was poured into a plastic petri dish (90 mm diameter), and a primary leaf piece of a kidney bean plant was placed thereon. 15 first instar larvae of T. palmi were inoculated thereon.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• the diluent was sprayed on the leaf piece of the kidney bean plant.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality of T. palmi was examined 2 days after that, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds with compound numbers shown in Table 9 were tested for efficacy against T. palmi at a compound concentration of 125 ppm. All compounds showed an insecticidal rate of 80% or more. The insecticidal rate of the comparative compound A was 0%.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• Cabbage leaves were immersed in the diluent for 30 seconds.
• the cabbage leaves were air dried and placed in a petri dish, and five second instar larvae of diamide-based insecticide-resistant P. xylostella were released.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated when 3 days passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds with compound numbers shown in Table 10 were tested for efficacy against diamide-based insecticide-resistant P. xylostella .
• the compounds showed an insecticidal rate of 80% or more against diamide-based insecticide-resistant P. xylostella .
• the insecticidal rate of the comparative compound A was 0%.
• the insecticidal rate of a flubendiamide wettable powder (trade name: Phoenix granular wettable powder) at 50 ppm was 0%, which served as a control experiment.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm.
• Cabbage leaves were immersed in the diluent for 30 seconds.
• the cabbage leaves were air dried and placed in a petri dish, and 8 second instar larvae of benzoylurea-based insecticide-resistant H. armigera were inoculated.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated when 3 days passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice.
• the compounds with compound numbers shown in Table 11 were tested for efficacy against benzoylurea-based insecticide-resistant H. armigera .
• the compounds showed an insecticidal rate of 80% or more against benzoylurea-based insecticide-resistant H. armigera .
• the insecticidal rate of the comparative compound A was 0%.
• the insecticidal rate of a teflubenzuron emulsion (trade name: Nomolt emulsion) at 25 ppm was 0%, which served as a control experiment.
• Cabbages raised to 2 leaf stage were pulled out from the soil, and after washing off the soil attached to the roots with tap water, hydroponically cultivated for 4 days by soaking the roots in tap water.
• the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 7.8 ppm, thereby preparing a drug solution for the root dipping test.
• the hydroponic cultivation was continued in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% with the roots of cabbage seedlings being soaked in the drug solution.
• the petri dish was left to stand in a thermostatic chamber at a temperature of 25° C. and a humidity of 60% during the test period. Mortality was evaluated after 3 days, and the insecticidal rate was calculated. The test was repeated twice.
• the pyridinium salts of the present invention including the compounds that are not shown in examples are compounds having the effects of pest control, acaricidal effects, and in particular, insecticidal effects and the like.
• a pyridinium salt which is excellent in pest control activity, in particular, insecticidal activity and/or acaricidal activity, excellent in safety and can be synthesized in an industrially favorable manner.
• a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or an endoparasite control- or exterminating agent containing a pyridinium salt as an active ingredient it is possible to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or an endoparasite control- or exterminating agent containing a pyridinium salt as an active ingredient.

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